二溴三苯基膦 → 5-Bromo-3-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 78615

反应方程式

HRID 78615 反应方程式
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH:19][NH2:20])=O.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:8][C:5]1[N:4]=[C:3]([C:9]2[O:11][C:17]([C:13]3[S:12][CH:16]=[CH:15][CH:14]=3)=[N:19][N:20]=2)[C:2]([NH2:1])=[N:7][CH:6]=1

参与物

6

反应物 4

HCID 70579二溴三苯基膦HCID 730982-噻吩甲酰肼HCID 81531N,N-二异丙基乙胺3 次HCID 185216003-氨基-6-溴吡嗪-2-甲酸

产物 1

HCID 594719085-Bromo-3-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine收率 58.3%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂2 次

实验过程

3-amino-6-bromo-pyrazine-2-carboxylic acid (3.2 g, 14.68 mmol) and thiophene-2-carbohydrazide (2.152 g, 14.68 mmol) were suspended in acetonitrile (48.00 mL) at room temperature and dibromo(triphenyl)phosphorane (24.79 g, 58.72 mmol) was added, followed byadditional acetonitrile (16.00 mL). The reaction mixture turned bright yellow in colour and was stirred at room temperature for 1 h. After this time, the reaction mixture cooled in an icebath and DIPEA (7.209 g, 9.716 mL, 55.78 mmol) was added dropwise. The reaction mixture was stirred in the ice bath for 1 h and then additional DIPEA (2.277 g, 3.069 mL, 17.62 mmol) added and the reaction mixture stirred for left for 30 mins and further DIPEA (1.897 g, 2.557 mL, 14.68 mmol) added. The reaction mixture was stirred for 1 h and then filtered. The solid was washed with ether, isolated and then triturated with acetonitrile and washed with ether to give the product as a yellow solid (2.776 g, 57% yield); 1H NMR (400.0 MHz, DMSO) 7.35 (s, 1H), 7.80 (br s, 2H), 7.98 (m, 1H), 8.04 (m, 1H) and 8.45 (s, 1H); MS (ES+) 326.04

后处理

  1. additionwas added dropwise
  2. stirringthe reaction mixture stirred
  3. waitfor left for 30 mins
  4. stirringThe reaction mixture was stirred for 1 h
  5. filtrationfiltered
  6. washThe solid was washed with ether
  7. customisolated
  8. customtriturated with acetonitrile
  9. washwashed with ether

来源与证据

ORD记录
ord-539a504bdf254e19943bf081b9102183
来源数据集
uspto-grants-2014_09
专利号
US08841308B2

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